Sesquiterpenoids and phenolics from roots of Cichorium endivia var. crispum

Twelve known sesquiterpene lactones and the new guaianolide 10beta-methoxy-1alpha, 11beta,13-tetrahydrolactucin (10), together with three known phenolic acid esters were isolated from roots of Cichorium endivia var. crispum. The compounds were characterized by spectral methods.     

Sesquiterpenoids from Lactuca tatarica

A new guaianolide and a new eudesmanolide were isolated from Lactuca tatarica, as well as eight known sesquiterpenoids. The new compounds were elucidated on the basis of spectroscopic methods including IR, HRESIMS, 1D and 2D NMR, and the known compounds were established by comparing their physical data with those of the corresponding compounds in the literature.     

Sesquiterpene lactones from Pulicaria crispa

The investigation of Pulicaria crispa gave a new guaianolide identified as 1 beta,4 beta-dihydroxy-5 alpha (H)-guaia-10(14),11(13)-dien-8 alpha,12-olide (5).     

A cytotoxic 4α-methyl steroid from the aerial parts of Cimicifuga foetida L

A new 4α-methyl sterol, cimisterol A (1), together with five known compounds (2-6), were isolated from the aerial parts of Cimicifuga foetida L. The new compound's structure was determined with the help of extensive 1D and 2D NMR spectroscopy. Compound 1 exhibited broad-spectrum and potent cytotoxic activities against human HL-60, Jurkat, K562, U937, HepG-2, and SGC-7091 cell lines, with IC(50) values of 7.23, 2.89, 6.88, 3.38, 4.21, and 4.89 μM, respectively. Compound 3 showed moderate to weak activities to all cell lines, except for SGC-7091, having IC(50) values ranging from 13.37 to 17.72 μM. This is the first time a cytotoxic 4α-methyl sterol constituent was discovered from Cimicifuga spp.     

Norditerpenoids from Salvia castanea Diels f. pubescens

Three new norditerpenoids, castanol A-C (1-3), along with eighteen known diterpenoids, were isolated from Salvia castanea Diels f. pubescens. Their structures were elucidated by extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against five human cancer cell lines. The known compounds neo-tanshinlactone (12) and methyltanshinoate (17) exhibited significant cytotoxic activities against some cells.     

A new phenylpropanoid glycosides from Paris polyphylla var. yunnanensis

A new phenylpropanoid glycosides, 2-feruloyl-O-alpha-D-glucopyranoyl-(1'-->2)-3,6-O-feruloyl-beta-D-fructofuranoside, was isolated from the root of Paris polyphylla var. yunnanensis. The structure of the new glycoside was elucidated by spectroscopic methods. Cytotoxicity test showed that it has cytotoxic effect in a dose-dependent manner against the mice lung adenocarcinoma cell line (LA795).     

An unusual taxodione derivative from hairy roots of Salvia austriaca

From a root culture of Salvia austriaca, transformed with Agrobacterium rhizogenes, a new diterpenoid was isolated and its chemical structure was determined as 7-(2-oxohexyl)-11-hydroxy-6, 12-dioxo-7,9(11),13- abietatriene [= 7-(2-oxohexyl)-taxodione] on the basis of spectroscopic methods, especially 1D and 2D NMR, and by comparison with structurally related compounds. This compound represents a hitherto unknown 2-oxohexyl diterpenoid derivative. Cytotoxic studies revealed that the new compound exhibited high cytotoxic activity against three cancer cell lines with IC(50) values ranging from 0.63 to 0.72μM. Its cytotoxic effectiveness against the cancer cells was ten fold higher than that of taxodione.     

Cytotoxic activity of some Asarum plants

The cytotoxic activity against some tumor cell lines of 16 commonly used species of Asarum was evaluated in this study. All of these plants were widely used in Asian countries as traditional medicines or folk medicines. Their inhibitory activities against four tumor cell lines (HL-60, BGC-823, KB and Bel-7402) were compared. It was observed that 10 of the tested extracts (eight ethanol extracts and two water extracts) among 32 extracts of these plants showed cytotoxic activity. Those 95% ethanol extractions from A. caudigerellum, A. forbesii, A. inflatum and A. maximum exhibited the highest cytotoxic activity, and 95% ethanol extracts or water extracts of A. sieboldii var. seoulense, A. himalaicum, A. splendens and A. crispulatum showed selective activity against one or two cells among the tested tumor cells. This is the first report of Asarum plants possessing cytotoxic activity against tumor cell lines.     

Preliminary antiproliferative effects of some species of Terminalia, Combretum and Pteleopsis collected in Tanzania on some human cancer cell lines

Methanolic extracts (25 microug/ml) of species belonging to the genera of Combretum, Terminalia and Pteleopsis, collected during a field expedition in Tanzania in 1999, were screened for their antiproliferative and cytotoxic effects against three human cancer cell lines (HeLa, cervical carcinoma; T 24, bladder carcinoma; and MCF 7, breast carcinoma). A leaf extract of Combretum fragrans and a fruit extract of C. zeyheri gave the strongest antiproliferative and cytotoxic effects of all the twenty-four extracts screened in this investigation. In contrast to the highly powerful leaf extract of C. fragrans, the root extract of this species gave no cytotoxic effects against the investigated cancer cell lines at a concentration of 25 microg/ml. The other investigated species of Combretum and Terminalia differed greatly in their cytotoxic potential. Root extracts of Terminalia sambesiaca and T. sericea gave the strongest cytotoxic effects of the five species of Terminalia used in this study. Eight of the twenty-four investigated plant extracts showed pronounced cytotoxic effects (<30% proliferation compared to the control) against the T 24 bladder cancer cells, seven against the HeLa cells and four against the MCF 7 cells.     

Cytotoxic triterpene saponins from the leaves of Aralia elata

Phytochemical investigation of the leaves of Aralia elata has led to the isolation of four new compounds, 3-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl oleanolic acid (1), 3-O-[β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl (1→3)]-[β-D-glucopyranosyl (1→2)]-β-d-glucopyranosyl hederagenin 28-O-β-D-glucopyranoside (2), 3-O-{[β-D-glucopyranosyl (1→2)]-[β-d-glucopyranosyl (1→3)-β-d-glucopyranosyl (1→3)]-β-D-glucopyranosyl} oleanolic acid 28-O-β-D-glucopyranosyl ester (3) and 3-O-[β-D-glucopyranosyl (1→2)]-[β-D-glucopyranosyl (1→3)]-β-d-glucopyranosyl caulophyllogenin (4) and two known compounds, 3-O-[β-D-glucopyranosyl (1→3)-α-l-arabinopyranosyl]-echinocystic acid (5) and 3-O-α-L-arabinopyranosyl echinocystic acid (6). The structural determination was accomplished with spectroscopic analysis, in particular (13)C-NMR, 2D-NMR and HR-ESI-MS techniques. Compounds 1-6 were tested for their inhibition of the growth of HL60, A549 and DU145 cancer cells. Compound 1 showed significant cytotoxic activity against HL60 and A549 cancer cells with IC(50) values of 6.99μM and 7.93μM respectively. In addition, compounds 5 and 6 showed significant cytotoxic activity against HL60 cancer cells with IC(50) values of 5.75μM and 7.51μM, respectively.     

Bakkenolides from Petasites tatewakianus

A new bakkenolide and a known one were isolated from Petasites tatewakianus. The structure of the new compound was elucidated on the basis of spectroscopic methods including IR, EIMS, HRESIMS, 1D and 2D NMR, and the known compound was established by single crystal X-ray structural analysis. The in vitro cytotoxic activity of these two compounds against cultured human cervical carcinoma (HeLa), human breast cancer (MCF-7) and murine Lewis lung carcinoma (LLC) cell lines was also evaluated.     

A cytotoxic triterpenoid saponin from under-ground parts of Gypsophila pilulifera Boiss.& Heldr

A cytotoxic triterpenoid saponin was isolated from the under-ground parts of Gypsophila pilulifera Boiss.& Heldr. (Caryophyllaceae) naturally grow in the southwestern region of the Turkey. The structures of saponin was elucidated as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→4]-α-l-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester on the basis of extensive spectral analysis and chemical evidence. The separated triterpenoid saponin was isolated from Gypsophila pilulifera for the first time. The saponin compound displayed significant cytotoxicity against A549 cell line with IC(50) values >16μM.     

Triterpenes and steroids from the leaves of Aglaia exima (Meliaceae)

A study on the leaves of Aglaia exima led to the isolation of one new and seven known compounds: six triterpenoids and two steroids. Their structures were elucidated and analyzed mainly by using spectroscopic methods; 1D and 2D NMR, mass spectrometry, UV spectrometry and X-ray. All the triterpenoids and steroids were measured in vitro for their cytotoxic activities against eight cancer cell lines; lung (A549), prostate (DU-145), skin (SK-MEL-5), pancreatic (BxPC-3), liver (Hep G2), colon (HT-29), breast (MCF-7) and (MDA-MB-231). The new cycloartane triterpenoid, 24(E)-cycloart-24-ene-26-ol-3-one 1, showed potent cytotoxic activity against colon (HT-29) cancer cell line (IC₅₀ 11.5 μM).     

Two new triterpenoids from the bark of Eucalyptus exserta and their molluscicidal and cytotoxic activities

Two new triterpenoids, 2α-hydroxyurs-12-en-28-oic acid-3β-trans- isoferulate (1) and 2α, 3α, 24-trihydroxyolean-18-en-28-oic acid (2), together with three known triterpenoids (3-5) were isolated from the methanol extract of the bark of Eucalyptus exserta. Their structures were determined by spectroscopic means. Compounds 1, 2, and 5 exhibited molluscicidal activity against Pomacea canaliculata. All isolated compounds showed significant cytotoxic activity against Spodoptera litura (SL) cells.     

Cytotoxic and apoptotic effects of constituents from Millettia pachycarpa Benth

The aim of this study is to investigate the cytotoxic and apoptotic effects of constituents from the seeds of Millettia pachycarpa Benth. Fourteen compounds (1–14) including one novel chalcone (10) were isolated as active principles from Chinese herbal medicine M. pachycarpa Benth. Their structures were identified by using spectroscopic methods. All isolates were then evaluated for their cytotoxic effects against several cancer cell lines (HepG2, C26, LL2 and B16) with cisplatin as a positive control. And their apoptosis-inducing effects were tested against HeLa-C3 cells with taxol as a positive control. Both studies showed that compounds 1, 2, 7 and 10 demonstrated significant cytotoxic and apoptotic effects against cancer cells. Moreover, in the apoptosis assay the novel chalcone (10) showed strong apoptosis inducing effects at a concentration of 2 μM within 36 h. It was found to be the most potent apoptotic inducer of the compounds isolated from M. pachycarpa Benth.     

Two new lathyrane type diterpenoids from Euphorbia aellenii

Euphorbia aellenii Rech. f. (Euphorbiaceae) afforded a cytotoxic chloroform fraction from which two new esters of 6(17)-epoxylathyrol were identified (1 and 2). The structure of these compounds was elucidated by spectroscopic methods.     

Chemical constituents of the aerial part of Derris elliptica

A new coumaronochromone, 6,4'-dihydroxy-7,5' -dimethoxy-coumaronochromone (1), together with eleven known flavonoids (2-12) were isolated from the ethanol extract of the aerial part of Derris elliptica. Their structures were elucidated on the basis of spectroscopic analysis. Compounds 2, 4, 7, 8 and 9 exhibited moderate insecticidal activities against larvae of Aedes albopictus. All compounds showed strong cytotoxic activities against Spodoptera litura (SL) and Trichoplusia ni BTI-Tn-5B1-4 (Hi-5) cells comparison to positive control of rotenone.     

Sesquiterpenoids and phenolics from Taraxacum hondoense

Eleven sesquiterpene lactones, including the new guaianolide 11beta-hydroxydeacetylmatricarin-8-O-beta-glucopyranoside, along with four known phenolic glucosides were isolated from Taraxacum hondoense. The compounds were characterized by spectral methods.     

Four new phenanthrenes from Monomeria barbata Lindl

Three biphenanthrene compounds (1–3) and a triphenanthrene compound (4), together with six known biphenanthrene compounds (5–10), were isolated from the tubers of Monomeria barbata Lindl. Their structures were elucidated on the basis of extensive spectroscopic analysis (1D-, 2D-NMR, and HR-ESI-MS). These four new compounds were tested in vitro for the cytotoxic activity against liver carcinoma (HepG-2), promyelocytic leukaemia (HL60), ovarian carcinoma (Skov-3) and epidermoid carcinoma (A431) cancer cell lines and the antioxidant activity in DPPH radical scavenging. Compounds 1–4 exhibited significant cytotoxic activity against HepG-2 and HL60 cell lines, and potent antioxidant activity in DPPH radical scavenging.     

Flavonoids with antiplasmodial and cytotoxic activities of Macaranga triloba

A new flavanone derivative, malaysianone A (1), four prenylated flavanones, 6-prenyl-3'-methoxyeriodictyol (2), nymphaeol B (3), nymphaeol C (4) and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone (5), and two coumarins, 5,7-dihydroxycoumarin (6) and scopoletin (7), were isolated from the dichloromethane extract of the inflorescences of Macaranga triloba. The structures of these compounds were elucidated based on spectroscopic methods including nuclear magnetic resonance (NMR-1D and 2D), UV, IR and mass spectrometry. The cytotoxic activity of the compounds was tested against several cell lines, with 5 inhibiting very strongly the growth of HeLa and HL-60 cells (IC(50): 1.3 μg/ml and 3.3 μg/ml, respectively). Compound 5 also showed strong antiplasmodial activity (IC(50): 0.06 μM).